Sign Up Submit Enquiry

Investigation of structural and conformational stability, electronic transition, NLO, FMO, and DSSC parameters of trans-dichloro-nitro chalcone isomers: a DFT insight

Home Investigation of structural and conformational stability, electronic transition, NLO, FMO, and DSSC parameters of trans-dichloro-nitro chalcone isomers: a DFT insight

Related Articles

Contact us

Article Content

Abstract

The density functional theory (DFT) with Becke’s three-parameter Lee–Yang–Parr (B3LYP) hybrid functional and the 6-311G(d,p) basis set was utilized to investigate the structural and conformational stability, the energies of the highest occupied molecular orbital (HOMO), and lowest unoccupied molecular orbital (LUMO), as well as related reactivity parameters, electrostatic potential, electronic transitions, nonlinear optical (NLO) properties, and dye-sensitized solar cell (DSSC) characteristics of six isomers of (E)-3-(i,j-dichlorophenyl)-1-(4′-nitrophenyl)prop-2-en-1-one, where i, j = 2–6 and i ≠ j. The s-cis conformers are more stable than the s-trans conformers. The syn conformers are more stable for five of the isomers than their anti-syn counterparts. The (3,5) isomer was the most stable among the isomers. All isomers demonstrated the ability to inject and recover electrons. The (2,5) isomer exhibited the highest exciton binding energy, while the (3,4) isomer showed the lowest dye regeneration driving force. The highest open-circuit voltage was observed for the (2,6) and (2,3) isomers. The (3,4) isomer had the highest light-harvesting efficiency, whereas the (2,5) isomer had the lowest. All chalcones exhibit higher first-order hyperpolarizability β values than urea, with the anti-(3,4) isomer having the highest β and the smallest (HOMO–LUMO) energy gap. TD-DFT (B3LYP/6-311G(d,p)) in the gas phase reveals that the chalcones display two UV bands. Band 1 arises from the electronic transition between the HOMO and LUMO. However, band 2 consists of electron excitation from HOMO and HOMO-2 to LUMO + 1. The chalcones investigated show promise as candidates for NLO and DSSC applications.

Graphical abstract

Explore related subjects

Discover the latest articles and news from researchers in related subjects, suggested using machine learning.

  • Computational Chemistry
  • Fullerenes
  • Organic Chemistry
  • Physical Chemistry
  • Supramolecular Chemistry
  • Theoretical Chemistry

Data availability

Data are provided in the manuscript and supplementary information files. No datasets were generated or analysed during the current study.

References

  1. Grätzel, M.: Dye-sensitized solar cells. J. Photochem. Photobiol. C Photochem. Rev. 4, 145–153 (2003)

    Google Scholar

  2. Hagfeldt, A., Boschloo, G., Sun, L., Kloo, L., Pettersson, H.: Dye-sensitized solar cells. Chem. Rev. 110, 6595–6663 (2010)

    Google Scholar

  3. Kumara, N.T.R.N., Lim, A., Lim, C.M., Petra, M.I., Ekanayake, P.: Recent progress and utilization of natural pigments in dye sensitized solar cells: a review. Renew. Sustain. Energy Rev. 78, 301–317 (2017). https://doi.org/10.1016/j.rser.2017.04.075

    Article Google Scholar

  4. Nizar, S.N.A.M., Rosli, M.M., Samsuri, S.A.M., Razak, I.A., Arshad, S.: Studies in the influence of D-π-A pyrenyl chalcone containing methoxy substitution as dye-sensitizer in DSSC. IOP Conf. Ser. Earth Environ. Sci. (2023). https://doi.org/10.1088/1755-1315/1281/1/012028

    Article Google Scholar

  5. Conradie, J.: Effective dyes for DSSCs–Important experimental and calculated parameters. Energy Nexus. 13, 100282 (2024). https://doi.org/10.1016/j.nexus.2024.100282

    Article Google Scholar

  6. El Mzioui, S., Bouzzine, S.M., Bourass, M., Naciri Bennani, M., Hamidi, M.: A theoretical investigation of the optoelectronic performance of some new carbazole dyes. J. Comput. Electron. 18, 951–961 (2019). https://doi.org/10.1007/s10825-019-01339-x

    Article Google Scholar

  7. Obasuyi, A.R., Glossman-Mitnik, D., Flores-Holguín, N.: Electron injection in anthocyanidin and betalain dyes for dye-sensitized solar cells: a DFT approach. J. Comput. Electron. 18, 396–406 (2019). https://doi.org/10.1007/s10825-019-01331-5

    Article Google Scholar

  8. Fadili, D., Bouzzine, S.M., Hamidi, M.: Effects of adding cyanovinyl moiety on the photovoltaic DSSCs phosphonic acid based cells. J. Comput. Electron. 19, 1629–1644 (2020). https://doi.org/10.1007/s10825-020-01546-x

    Article Google Scholar

  9. Rosli, M.M., Anizaim, A.H., Nizar, S.N.A.M., Razak, I.A., Arshad, S.: Designing ferrocenyl thiophene chalcones as light harvester candidates for dye-sensitized solar cells. J. Organomet. Chem. 1022, 123415 (2024). https://doi.org/10.1016/J.JORGANCHEM.2024.123415

    Article Google Scholar

  10. Nizar, S.N.A.M., Rosli, M.M., Samsuri, S.A.M., Razak, I.A., Arshad, S.: Involvement of halogen and polyaromatic substituents in chalcone derivatives as dye sensitizers in solar cell applications. New J. Chem. 47, 5804–5815 (2023). https://doi.org/10.1039/D2NJ05937A

    Article Google Scholar

  11. Nassar, M.F., Abdulmalek, E., Ismail, M.F., Ahmad, S.A.A.: Enhancing the performance of pyridyl carboxamide-N,N-dimethyl amino chalcone (PCC) as a dye sensitizer for dye-sensitized solar cells (DSSCs) through the incorporation of electron donor moieties. Int. J. Electrochem. Sci. 19, 100715 (2024). https://doi.org/10.1016/j.ijoes.2024.100715

    Article Google Scholar

  12. Pina, V., da Costa Duarte, R., Vesga-Hernández, C., dos Santos Carvalho, R., Melo, D.G., Pedrozo-Penãfiel, M.J., Barreto, A.R.J., dos Santos, A.M., Dal-Bó, A.G., Aucélio, R.Q., Cremona, M., Limberger, J.: Carboxy-substituted D-π-A arylated chalcones: Synthesis, photophysical properties and preliminary evaluation as photosensitizers for DSSCs. Opt. Mater. (Amst). 149, 115039 (2024). https://doi.org/10.1016/J.OPTMAT.2024.115039

  13. Mustafa, M.N., Hussain, F., Hussain, M., Hussain, R., Ayub, K., Muhammad, S., Khan, M.U., Ehsan, M., Adnan, M.: Elucidating the potential of nonlinear optical behavior of azo dyes for advanced laser-based technologies. Adv. Theory Simul. (2025). https://doi.org/10.1002/adts.202401202

    Article Google Scholar

  14. Boyd, R.W.: Nonlinear Optics (3rd edn). (2019)

  15. Agrawal, G.P.: Nonlinear Fiber Optics (6th edn). Academic Press (2019)

  16. Runowski, M., Woźny, P., Martín, I.R., Soler-Carracedo, K., Zheng, T., Hemmerich, H., Rivera-López, F., Moszczyński, J., Kulpiński, P., Feldmann, S.: Multimodal optically nonlinear nanoparticles exhibiting simultaneous higher harmonics generation and upconversion luminescence for anticounterfeiting and 8-bit optical coding. Adv. Funct. Mater. 34, 1–10 (2024). https://doi.org/10.1002/adfm.202307791

    Article Google Scholar

  17. Marder, S.R.: Organic nonlinear optical materials: where we have been and where we are going. Chem. Commun. (2006). https://doi.org/10.1039/b512646k

    Article Google Scholar

  18. Hadji, D., Bensafi, T.: Deeper insights on the nonlinear optical properties of O-acylated pyrazoles. J. Electron. Mater. 53, 1868–1883 (2024). https://doi.org/10.1007/s11664-024-10954-9

    Article Google Scholar

  19. Nourai, N.E.H., Sebih, F., Hadji, D., Allal, F.Z., Dib, S., Kambouche, N., Rolland, V., Bellahouel-Benzine, S.: Nonlinear optical and antimicrobial activity of N-acyl glycine derivatives. J. Mol. Liq. 398, 124260 (2024). https://doi.org/10.1016/j.molliq.2024.124260

    Article Google Scholar

  20. Hadji, D., Baroudi, B., Bensafi, T.: Nonlinear optical properties of azo sulfonamide derivatives. J. Mol. Model. (2024). https://doi.org/10.1007/s00894-024-05915-2

    Article Google Scholar

  21. Hadji, D., Haddad, B., Brandán, S.A., Panja, S.K., Paolone, A., Drai, M., Villemin, D., Bresson, S., Rahmouni, M.: Synthesis, NMR, Raman, thermal and nonlinear optical properties of dicationic ionic liquids from experimental and theoretical studies. J. Mol. Struct. 1220, 128713 (2020). https://doi.org/10.1016/j.molstruc.2020.128713

    Article Google Scholar

  22. Hadji, D.: Phosphates branching effect on the structure, linear and NLO properties of linear phosphazenes. Mater. Chem. Phys. 262, 124280 (2021). https://doi.org/10.1016/j.matchemphys.2021.124280

    Article Google Scholar

  23. Gheribi, R., Hadji, D., Ghallab, R., Medjani, M., Benslimane, M., Trifa, C., Dénès, G., Merazig, H.: Synthesis, spectroscopic characterization, crystal structure, Hirshfeld surface analysis, linear and NLO properties of new hybrid compound based on tin fluoride oxalate and organic amine molecule (C12N2H9)2[SnF2(C2O4)2]2H2O. J. Mol. Struct. 1248, 131392 (2022). https://doi.org/10.1016/j.molstruc.2021.131392

    Article Google Scholar

  24. Bensafi, T., Hadji, D., Yahiaoui, A., Argoub, K., Hachemaoui, A., Kenane, A., Baroudi, B., Toubal, K., Djafri, A., Benkouider, A.M.: Synthesis, characterization and DFT calculations of linear and NLO properties of novel (Z)-5-benzylidene-3-N(4-methylphenyl)-2-thioxothiazolidin-4-one. J. Sulfur Chem. 42, 645–663 (2021). https://doi.org/10.1080/17415993.2021.1951729

    Article Google Scholar

  25. Hadji, D., Benmohammed, A., Mouchaal, Y., Djafri, A.: Synthesis and characterization of novel thiosemicarbazide for nonlinear optical applications: combined experimental and theoretical study. Rev. Roum. Chim. 68, 463–471 (2023). https://doi.org/10.33224/rrch.2023.68.9.07

    Article Google Scholar

  26. Zyss, J., Ledoux, I.: Nonlinear optics in multipolar media: theory and experiments. Chem. Rev. 94, 77–105 (1994). https://doi.org/10.1021/cr00025a003

    Article Google Scholar

  27. Agilandeshwari, R., Meenatchi, V., Meenakshisundaram, S.P.: Synthesis, growth, structure and characterization of chalcone crystal: a novel organic NLO material. J. Mol. Struct. 1118, 356–366 (2016). https://doi.org/10.1016/j.molstruc.2016.02.099

    Article Google Scholar

  28. Patil, P.S., Maidur, S.R., Jahagirdar, J.R., Chia, T.S., Quah, C.K., Shkir, M.: Crystal structure, spectroscopic analyses, linear and third-order nonlinear optical properties of anthracene-based chalcone derivative for visible laser protection. Appl. Phys. B Lasers Opt. 125, 1–13 (2019). https://doi.org/10.1007/s00340-019-7275-z

    Article Google Scholar

  29. Shruthi, C., Ravindrachary, V., Guruswamy, B., Prasad, D.J., Goveas, J., Kumara, K., Lokanath, N.K.: Molecular structure, Hirshfeld surface and density functional theoretical analysis of a NLO active chalcone derivative single crystal—a quantum chemical approach. J. Mol. Struct. 1228, 129739 (2021). https://doi.org/10.1016/j.molstruc.2020.129739

    Article Google Scholar

  30. Arshad, M.N., Al-Dies, A.A.M., Asiri, A.M., Khalid, M., Birinji, A.S., Al-Amry, K.A., Braga, A.A.C.: Synthesis, crystal structures, spectroscopic and nonlinear optical properties of chalcone derivatives: a combined experimental and theoretical study. J. Mol. Struct. 1141, 142–156 (2017). https://doi.org/10.1016/j.molstruc.2017.03.090

    Article Google Scholar

  31. Shkir, M., AlFaify, S., Arora, M., Ganesh, V., Abbas, H., Yahia, I.S.: A first principles study of key electronic, optical, second and third order nonlinear optical properties of 3-(4-chlorophenyl)-1-(pyridin-3-yl) prop-2-en-1-one: a novel D- π -A type chalcone derivative. J. Comput. Electron. 17, 9–20 (2018). https://doi.org/10.1007/s10825-017-1050-3

    Article Google Scholar

  32. Nehru, J., Subramani, S., Rosli, M.M., Zainuri, D.A., Subramanian, U.M., Marappan, V., Savaridasson, J.K., Kasthuri, B., Arshad, S., Alsaee, S.K., Venkatachalam, R., Madhukar, H.: Shining light on chalcone compounds: A comprehensive exploration through optical and thermal studies. Opt. Mater. (Amst). 149, 115069 (2024). https://doi.org/10.1016/j.optmat.2024.115069

  33. Nizar, S.N.A.M., Ab Rahman, S.N.F., Zaini, M.F., Anizaim, A.H., Abdul Razak, I., Arshad, S.: The photovoltaic performance of sensitizers for organic solar cells containing fluorinated chalcones with different halogen substituents. Crystals 11, 1–18 (2021)

    Google Scholar

  34. Marcovicz, C., Camargo, G. dos A., Scharr, B., Sens, L., Levandowski, M.N., Rozada, T. de C., Castellen, P., Inaba, J., de Oliveira, R.N., Miné, J.C., Corrêa, S. de A.P., Allegretti, S.M., Fiorin, B.C.: Schistosomicidal evaluation of synthesized bromo and nitro chalcone derivatives. J. Mol. Struct. 1258, 132647 (2022). https://doi.org/10.1016/j.molstruc.2022.132647

  35. Shainyan, B.A., Sigalov, M.V.: Hydrogen bonding-assisted transformations of cyclic chalcones: E/Z-isomerization, self-association and unusual tautomerism. Russ. Chem. Rev. 91, RCR5035 (2022). https://doi.org/10.1070/rcr5035

    Article Google Scholar

  36. Nithya, R., Santhanamoorthi, N., Kolandaivel, P., Senthilkumar, K.: Structural and spectral properties of 4-bromo-1-naphthyl chalcones: a quantum chemical study. J. Phys. Chem. A 115, 6594–6602 (2011). https://doi.org/10.1021/jp1098393

    Article Google Scholar

  37. Xue, Y., Gong, X.: The conformational, electronic and spectral properties of chalcones: a density functional theory study. J. Mol. Struct. Theochem. 901, 226–231 (2009). https://doi.org/10.1016/j.theochem.2009.01.034

    Article Google Scholar

  38. Hameed, S.A.: Electronic structure of some chalcone derivatives. I. Ground state geometric parameters and charge density distributions, AM1-MO treatment. JKAU Sci. 18, 13–25 (2006)

    Google Scholar

  39. Carvalho, P.S., Custodio, J.M.F., Vaz, W.F., Cirilo, C.C., Cidade, A.F., Aquino, G.L.B., Campos, D.M.B., Cravo, P., Coelho, C.J., Oliveira, S.S., Camargo, A.J., Napolitano, H.B.: Conformation analysis of a novel fluorinated chalcone. J. Mol. Model. (2017). https://doi.org/10.1007/s00894-017-3245-8

    Article Google Scholar

  40. Zainuri, D.A., Abdullah, M., Arshad, S., Aziz, M.S.A., Krishnan, G., Bakhtiar, H., Razak, I.A.: Crystal structure, spectroscopic and third-order nonlinear optical susceptibility of linear fused ring dichloro-substituent chalcone isomers. Opt. Mater. (Amst.) 86, 32–45 (2018). https://doi.org/10.1016/j.optmat.2018.09.032

    Article Google Scholar

  41. Gandhimathi, R., Vinitha, G., Dhanasekaran, R.: Effect of substituent position on the properties of chalcone isomer single crystals. J. Cryst. Process Technol. 3, 148–155 (2013)

    Google Scholar

  42. Ashburn, B.O.: Computational analysis of a series of chlorinated chalcone derivatives. Comput. Chem. 07, 106–120 (2019). https://doi.org/10.4236/cc.2019.74008

    Article Google Scholar

  43. Hussein, H.A., Fadhil, G.F.: Theoretical investigation of para amino-dichloro chalcone isomers, part I: A DFT structure—stability study. J. Phys. Org. Chem. 33, 1–15 (2020). https://doi.org/10.1002/poc.4073

    Article Google Scholar

  44. Yousif, A.A., Fadhil, G.F.: DFT of para methoxy dichlorochalcone isomers. Investigation of structure, conformation, FMO, charge, and NLO properties. Chem. Data Collect. 31, 100618 (2021). https://doi.org/10.1016/j.cdc.2020.100618

    Article Google Scholar

  45. Hadji, D., Champagne, B.: First principles investigation of the polarizability and first hyperpolarizability of anhydride derivatives. Chem. Africa. (2019). https://doi.org/10.1007/s42250-019-00060-3

    Article Google Scholar

  46. Hadji, D., Rahmouni, A., Hammoutène, D., Zekri, O.: First theoretical study of linear and nonlinear optical properties of diphenyl ferrocenyl butene derivatives. J. Mol. Liq. 286, 110939 (2019). https://doi.org/10.1016/j.molliq.2019.110939

    Article Google Scholar

  47. Hadji, D., Rahmouni, A.: Molecular structure, linear and nonlinear optical properties of some cyclic phosphazenes: a theoretical investigation. J. Mol. Struct. 1106, 343–351 (2016). https://doi.org/10.1016/j.molstruc.2015.10.033

    Article Google Scholar

  48. Baroudi, B., Argoub, K., Hadji, D., Benkouider, A.M., Toubal, K., Yahiaoui, A.: Synthesis and DFT calculations of linear and nonlinear optical responses of novel 2-thioxo-3-N, (4-methylphenyl ) thiazolidine-4 one. J. Sulfur. Chem. (2020). https://doi.org/10.1080/17415993.2020.1736073

    Article Google Scholar

  49. Cherif, F.Y., Hadji, D., Benhalima, N.: Molecular structure, linear, and nonlinear optical properties of piperazine-1,4- diium bis 2,4,6-trinitrophenolate: a theoretical investigation. Phys. Chem. Res. 11, 33–48 (2023). https://doi.org/10.22036/pcr.2022.330752.2035

    Article Google Scholar

  50. Gaussian 09, R.D. 0., M. J. Frisch, G. W. Trucks, H. B. Schlegel, G.E.S., M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, B.M., G. A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P.H., A. F. Izmaylov, J. Bloino, G. Zheng, J. L. Sonnenberg, M.H., M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T.N., Y. Honda, O. Kitao, H. Nakai, T. Vreven, J. A. Montgomery, J., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E.B., K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J.N., K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J.T., M. Cossi, N. Rega, J. M. Millam, M. Klene, J. E. Knox, J.B.C., V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E.S., O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J.W.O., R. L. Martin, K. Morokuma, V. G. Zakrzewski, G.A.V., P. Salvador, J. J. Dannenberg, S. Dapprich, A.D.D., O. Farkas, J. B. Foresman, J. V. Ortiz, J.C., and D. J. Fox, Gaussian, Inc., Wallingford CT, 2013.: Gaussian 09, (2013)

  51. Dennington, R., Keith, T.A., Millam, J.M.: GaussView 6.0. 16, (2016)

  52. Origin(Pro), Version 2019b. OriginLab Corporation, Northampton, MA, USA

  53. ChemDraw Professional, Version 23.1.1.3, revvity signals software, inc

  54. Merouane, A., Mostefai, A., Hadji, D., Rahmouni, A., Bouchekara, M.: Theoretical insights into the static chemical reactivity and NLO properties of some conjugated carbonyl compounds : case. Monatshefte für Chemie – Chem. Mon. (2020). https://doi.org/10.1007/s00706-020-02653-y

    Article Google Scholar

  55. Abu-awwad, F., Politzer, P.: Variation of parameters in becke-3 hybrid exchange-correlation functional variation of parameters in becke-3 hybrid exchange-correlation functional. J. Comput. Chem. 21, 227–238 (2000). https://doi.org/10.1002/(SICI)1096-987X(200002)21

    Article Google Scholar

  56. Hantosh, L.A., Sami, S.A., Fadhil, G.F.: Structure-stability and energy storage capacity of para acetyl-dichloro chalcone and chromen isomers : a density functional theory investigation. Orient. J. Chem. 40, 1774–1785 (2024)

    Google Scholar

  57. Politzer, P., Murray, J.S.: Molecular electrostatic potentials: Significance and applications. Chem. React. Confin. Syst. Theory Model Appl. (2021). https://doi.org/10.1002/9781119683353.ch7

    Article Google Scholar

  58. de Paula, R.L.G., Carvalho, F.B., D’Oliveira, G.D.C., Duarte, V.S., Santin, L.G., Pérez, C.N., Oliveira, S.S., Napolitano, H.B.: Synthesis, crystal structure and molecular modeling of a novel chalcone-quinolone hybrid. J. Mol. Struct. 1217, 128355 (2020). https://doi.org/10.1016/j.molstruc.2020.128355

    Article Google Scholar

  59. Sirleto, L., Righini, G.C.: An introduction to nonlinear integrated photonics devices: nonlinear effects and materials. Micromachines 14, 1–25 (2023). https://doi.org/10.3390/mi14030604

    Article Google Scholar

  60. Naik, V.S., Patil, P.S., Gummagol, N.B., Wong, Q.A., Quah, C.K., Jayanna, H.S.: Crystal structure, linear and nonlinear optical properties of three thiophenyl chalcone derivatives: a combined experimental and computational study. Opt. Mater. (Amst.) 110, 110462 (2020). https://doi.org/10.1016/j.optmat.2020.110462

    Article Google Scholar

  61. Chen, R., Xu, K., Li, Q., Ma, J., Wang, T., Zhang, Z., Mu, X., Xuan, F., Cao, L., Teng, B.: Synthesis and characterization of a new chalcone-based nonlinear optical crystal: BBC. J. Mol. Struct. 1293, 136320 (2023). https://doi.org/10.1016/j.molstruc.2023.136320

    Article Google Scholar

  62. Aneesa, V.M., Safna Hussan, K.P., Lekshmi, S., Babu, T.D., Muraleedharan, K.: Analysis of non-linear optical properties of phytochemical photosensitizers in cancer photodynamic therapy by quantum computational. Results Chem. 8, 101580 (2024). https://doi.org/10.1016/j.rechem.2024.101580

    Article Google Scholar

  63. Mishra, A.K., Tewari, S.P.: Density functional theory calculations of spectral, NLO, reactivity, NBO properties and docking study of Vincosamide-N-Oxide active against lung cancer cell lines H1299. SN Appl. Sci. 2, 1–13 (2020). https://doi.org/10.1007/s42452-020-2842-9

    Article Google Scholar

  64. Chidan Kumar, C.S., Quah, C.K., Balachandran, V., Fun, H.K., Asiri, A.M., Chandraju, S., Karabacak, M.: Synthesis, single crystal structure, spectroscopic characterization and molecular properties of (2E)-3-(2,6-dichlorophenyl)-1-(3,4-dimethoxyphenyl)prop-2-en-1-one. J. Mol. Struct. (2016). https://doi.org/10.1016/j.molstruc.2016.02.089

    Article Google Scholar

  65. Shinde, S.S., Sreenath, M.C., Chitrambalam, S., Joe, H., Sekar, N.: Non-linear optical properties of disperse blue 354 and disperse blue183 by DFT and Z-Scan technique. Polycycl. Aromat. Compd. (2019). https://doi.org/10.1080/10406638.2019.1686404

    Article Google Scholar

  66. Chaitanya, K., Ju, X.H., Heron, B.M., Gabbutt, C.D.: Vibrational spectra and static vibrational contribution to first hyperpolarizability of naphthopyrans – a combined experimental and DFT study. Vib. Spectrosc. 69, 65–83 (2013). https://doi.org/10.1016/j.vibspec.2013.09.010

    Article Google Scholar

  67. Niu, R., Wang, Y., Wu, X., Chen, S., Zhang, X., Song, Y.: D-π-A-type pyrene derivatives with different push-pull properties: broadband absorption response and transient dynamic analysis. J. Phys. Chem. C 124, 5345–5352 (2020). https://doi.org/10.1021/acs.jpcc.9b11667

    Article Google Scholar

  68. Teo, K.Y., Tiong, M.H., Wee, H.Y., Jasin, N., Liu, Z.Q., Shiu, M.Y., Tang, J.Y., Tsai, J.K., Rahamathullah, R., Khairul, W.M., Tay, M.G.: The influence of the push-pull effect and a π-conjugated system in conversion efficiency of bis-chalcone compounds in a dye sensitized solar cell. J. Mol. Struct. 1143, 42–48 (2017). https://doi.org/10.1016/j.molstruc.2017.04.059

    Article Google Scholar

  69. Abbo, H.S., Hung Lai, C., Titinchi, S.J.J.: Substituent and solvent effects on UV-visible absorption spectra of chalcones derivatives: experimental and computational studies. Spectrochim. Acta. Part A Mol. Biomol. Spectrosc. 303, 123180 (2023). https://doi.org/10.1016/j.saa.2023.123180

    Article Google Scholar

  70. Szmant, H.H., Basso, A.J.: The absorption spectra of substituted chalcones. J. Am. Chem. Soc. 74, 4397–4400 (1952). https://doi.org/10.1021/ja01137a047

    Article Google Scholar

  71. Xue, Y., Mou, J., Liu, Y., Gong, X., Yang, Y., An, L.: An ab initio simulation of the UV/Visible spectra of substituted chalcones. Cent. Eur. J. Chem. 8, 928–936 (2010). https://doi.org/10.1002/qua

    Article Google Scholar

  72. Lipkowitz, K.B., Boyd, D.B., Larter, R., Cundari, T.R.: Reviews in Computational Chemistry Volume 20. In: Wiley, pp. 484 (2004)

  73. Miar, M., Shiroudi, A., Pourshamsian, K., Oliaey, A.R., Hatamjafari, F.: Theoretical investigations on the HOMO–LUMO gap and global reactivity descriptor studies, natural bond orbital, and nucleus-independent chemical shifts analyses of 3-phenylbenzo[d]thiazole-2(3H)-imine and its para-substituted derivatives: Solvent and subs. J. Chem. Res. 45, 147–158 (2021). https://doi.org/10.1177/1747519820932091

    Article Google Scholar

  74. Masnabadi, N., Thalji, M.R., Alhasan, H.S., Mahmoodi, Z., Soldatov, A.V., Ali, G.A.M.: Structural, electronic, reactivity, and conformational features of 2,5,5-Trimethyl-1,3,2-diheterophosphinane-2-sulfide, and its derivatives: DFT, MEP, and NBO calculations. Molecules 27, 4011 (2022)

    Google Scholar

  75. Lavanya, M., Mahalakshmi, C.M.: DFT calculations on molecular structure, homo lumo study reactivity descriptors of triazine derivative. Int. Res. J. Educ. Technol. 5, 49–52 (2023)

    Google Scholar

  76. Asiri, A.M., Ersanlı, C.C., Şahin, O., Arshad, M.N., Hameed, S.A.: Molecular structure, spectroscopic and quantum chemical studies of 1’,3’,3’-trimethylspiro[benzo[f]chromene-3,2’-indoline. J. Mol. Struct. (2016). https://doi.org/10.1016/j.molstruc.2016.01.086

    Article Google Scholar

  77. Hussein, H.A., Fadhil, G.F.: Theoretical investigation of para amino-dichloro chalcone isomers. Part II: a DFT structure-stability study of the FMO and NLO properties. ACS Omega 8, 4937–4953 (2023). https://doi.org/10.1021/acsomega.2c07148

    Article Google Scholar

  78. Hantosh, L.A.: Structure-stability, energy storage capacity, frontier molecular orbitals, and dye sensitized solar energy study of the para acetyl- dichloro chalcone and chromene isomers : a DFT investigation (2025)

  79. Odey, J.O., Louis, H., Agwupuye, J.A., Moshood, Y.L., Bisong, E.A., Brown, O.I.: Experimental and theoretical studies of the electrochemical properties of mono azo dyes derived from 2-nitroso-1- naphthol, 1-nitroso-2-naphthol, and C.I disperse yellow 56 commercial dye in dye-sensitized solar cell. J. Mol. Struct. 1241, 130615 (2021). https://doi.org/10.1016/j.molstruc.2021.130615

    Article Google Scholar

  80. Fei, E.T.L., Biswas, J., Datta, B., Kumar, D.: Computational studies of diindole-based molecules for organic bulk heterojunction solar devices using DFT and TD-DFT calculations. Struct. Chem. 32, 1973–1984 (2021). https://doi.org/10.1007/s11224-021-01777-z

    Article Google Scholar

  81. Babu, N.S.: DFT and TD-DFT studies of new triphenylamine-based (D-A-D) donor materials for high-efficiency organic solar cells. Mater. Adv. (2022). https://doi.org/10.1039/d2ma00048b

    Article Google Scholar

  82. Benmohammed, A., Hadji, D., Mouchaal, Y., Djafri, A.: Synthesis and characterization of novel chalcone with good nonlinear optical properties. Chem. Africa. (2024). https://doi.org/10.1007/s42250-024-01143-6

    Article Google Scholar

Download references

Acknowledgements

Hazhi Hasan Hussein would like to thank the University of Duhok for the PhD scholarship that enabled him to complete this article.

Funding

This research has received no funding.

Author information

Authors and Affiliations

  1. College of Science, Department of Chemistry, University of Duhok, Zakho Street 38, Duhok, Kurdistan Region, 1006AJ, Iraq

    Hazhi Hasan Hussein & Ghazwan Faisal Fadhil

Contributions

H. H. H. did all the calculations. H. H. H. and G. F. F. contributed equally to the analysis and writing of the article.

Corresponding author

Correspondence to Ghazwan Faisal Fadhil.

Ethics declarations

Competing interest

The authors declare no competing interests.

Ethical approval

This research is not applicable to any human or animal studies.

Additional information

Publisher’s Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 7255 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and permissions

About this article

Cite this article

Hussein, H.H., Fadhil, G.F. Investigation of structural and conformational stability, electronic transition, NLO, FMO, and DSSC parameters of trans-dichloro-nitro chalcone isomers: a DFT insight. J Comput Electron 24, 140 (2025). https://doi.org/10.1007/s10825-025-02378-3

Download citation

  • Received 
  • Accepted 
  • Publishe  d
  • DOI  https://doi.org/10.1007/s10825-025-02378-3

Keywords

  • Chalcone isomer stability
  • DFT
  • ESP
  • Electronic transition
  • NLO
  • DSSC

 

Copyright © All rights reserved Designed and Developed by Digital Flavers

WhatsApp